Hydrochloric Acid → 5-(4-Iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine

HRID 19610Notes

Reaction equation

HRID 19610 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[S:14])[N:11]3[N:15]=[CH:16][CH:17]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:19]O>[OH-].[Na+].CI>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:19])[N:11]3[N:15]=[CH:16][CH:17]=[C:10]3[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178527901HCID 178527901, compound2×

Product 1

HCID 673194195-(4-Iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidineYield 62%

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5-(4-iodo-phenyl)-6H-pyrazolo[1,5-c]pyrimidine-7-thione (compound E1)(2.09 g) in 2M aqueous NaOH (3 ml) and methanol (40 ml), methyl iodide (0.376 ml) is added at ambient temperature. After 30 min at this temperature further methyl iodide (0.376 ml) is added. After 60 min the mixture is neutralized with 2M hydrochloric acid and evaporated. The residue is partitioned between dichloromethane and water and the organic phase is washed twice with water. The organic phase is dried over sodium sulfate and the crude product is purified by silica gel flash chromatography. A nearly colorless solid (1.35 g, 62%) is obtained.

Workup

  1. customevaporated
  2. customThe residue is partitioned between dichloromethane and water
  3. washthe organic phase is washed twice with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-b247128ee3224d0c91cfed75187bcfd9
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Reaction notes

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